HCID 178463187, compound → HCID 178463186, compound

HRID 1014959Notes

Reaction equation

HRID 1014959 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:45])=[N:25][C:26]=2[NH:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37]C(OC(C)(C)C)=O)[CH2:33][CH2:32]1)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.ClCCl>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:45])=[N:25][C:26]=2[NH:30][C@H:31]1[CH2:32][CH2:33][C@H:34]([NH2:37])[CH2:35][CH2:36]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 178463187HCID 178463187, compound2×

Product 1

HCID 178463186HCID 178463186, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(2R,3R,4R,5R)-2-(2-Chloro-6-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate (Intermediate 1) (12.49 g), was dissolved in trifluoroacetic acid—dichloromethane mixture (50:50; 40 ml). The mixture was stirred at room temperature for 1-2 h and then evaporated down in vacuo. The residue was partitioned between ethyl acetate and 2N aq.sodium bicarbonate solution, making sure the trifluoroacetic acid was neutralised. The organic phase was separated, washed with brine, dried (MgSO4), and evaporated down in vacuo, to give the title compound, 11.2 g.

Workup

  1. customevaporated down in vacuo
  2. customThe residue was partitioned between ethyl acetate and 2N aq
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated down in vacuo

Sources & evidence

ORD record
ord-f4d3e551798d40258d7c3bd79f472eed
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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